3-(p-Chlorophenyl)-3-cyclopropyl-2-fluoro-2-propen-1-ol → 2-Fluoro-3-cyclopropyl-3-(p-chlorophenyl)acrylaldehyde

HRID 1458392Notes

Reaction equation

HRID 1458392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:13]2[CH2:15][CH2:14]2)=[C:9]([F:12])[CH2:10][OH:11])=[CH:4][CH:3]=1>[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:13]2[CH2:14][CH2:15]2)=[C:9]([F:12])[CH:10]=[O:11])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 541655463-(p-Chlorophenyl)-3-cyclopropyl-2-fluoro-2-propen-1-ol

Product 1

HCID 540115002-Fluoro-3-cyclopropyl-3-(p-chlorophenyl)acrylaldehydeYield 60%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

Activated manganese(IV) oxide (101.25 g, 1.16 mol) is added to a solution of 3-(p-chlorophenyl)-3-cyclopropyl-2-fluoro-2-propen-l-ol, (E)- and (Z)- (26.4 g, 0.116 mol) in hexanes. The resultant reaction mixture is stirred at room temperature overnight, filtered through a pad of diatomaceous earth, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and an ethyl acetate/hexanes solution (1:9) gives the title product as an oil (15.8 g, 60%).

Workup

  1. customThe resultant reaction mixture
  2. filtrationfiltered through a pad of diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue

Sources & evidence

ORD record
ord-26091ab6a7ee4c72afe9cc52d1ebf46b
Source dataset
uspto-grants-1998_12
Patent number
US05849958

Reaction notes

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